


Dan "Joe Goldberg" Humphrey's First Date with Serena van der Woodsen

by princessrosebud98



Category: Gossip Girl (TV 2007), You (TV 2018)
Genre: F/M
Language: English
Status: Completed
Published: 2020-05-09
Updated: 2020-05-09
Packaged: 2021-03-02 23:26:42
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,215
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24095047
Author URL: https://archiveofourown.org/users/princessrosebud98/pseuds/princessrosebud98
Summary: A/N: The dialogue comes from Gossip Girl Season 1, Episode 5: “Dare Devil” and focuses on the lead-up to Dan and Serena’s first date. The portions in asterisks are meant to be read in the same ASMR, stream of consciousness style as Joe Goldberg’s inner monologues in the series You. In this fic, Dan Humphrey and Joe Goldberg are the same person; right now, Joe Goldberg has the alias of Dan Humphrey after being adopted by Rufus and Alison Humphrey in his elementary school years. Dan is just starting to show some of Joe’s later, token tendencies, but at this point he is pretty much harmless.
Relationships: Dan Humphrey/Serena van der Woodsen
Kudos: 6





	Dan "Joe Goldberg" Humphrey's First Date with Serena van der Woodsen

[DAN TRAVELS TO THE UPPER EAST SIDE, ENTERS “THE PALACE” AND TAKES THE ELEVATOR UP TO THE VAN DER WOODSEN ROOM]

**Today is finally the day. The day I get to go on my first date with you. Ever since I first saw you on the staircase at that party a few years ago I knew you, you, Serena van der Woodsen, were different from all these other shallow, heartless Upper East Siders. You deserve the very best, and today, I finally get to show you that the very best is, well, me. I’ve saved all of the money that I could to be able to take you on the date you deserve. My dad and Jenny ridiculed me for having to convert all of the change I’d been saving for years into cash to be able to take you out, but I’d do so much more just for the chance to sit across the table from you. I can’t wait to see you. I’ve got the perfect date planned for you – one that everyone else wouldn’t think I’m capable of. But not you; you know me. Tonight, I’m going to show you just how well I can infiltrate your world. I’m picking you up, per your request – it surprises me how traditional you are in some regards. It amazes me how you are able to survive every day in this posh prison – you are like Rapunzel in her tower, and I am here to save you, Serena.**

[DAN KNOCKS. SERENA OPENS THE DOOR]

DAN: Hey.

SERENA: Hey.

**You are beautiful, Serena. Absolutely breath-taking. If there were a beauty pageant between you and Helen of Troy, you would win in a landslide. But what are you wearing? Why did you decide today, of all days, to dress in jeans? Don’t get me wrong, Serena, anything you wear drives me wild, but why so casual on such an important day? Do you think I don’t have enough money to take you where you want to go? Did I tell you the wrong time?**

DAN: Hey, uh, am I early or

SERENA: Uh um No. No, I, uh, I'm just running late. Come in. Um excuse me while I go slip into something less comfortable.

**A little less comfortable mmmm… I can’t wait to see what that means…**

DAN: Sure, sure.

[SERENA GOES INTO HER ROOM TO CHANGE, LEAVING HER DOOR SLIGHTLY CRACKED]

SERENA: Talk to me while I change? 

DAN: I will.

**Serena… you tease. You left that door open on purpose, just for me to be able to get a glimpse of you changing. Your bare back… oh, you wanted me to see that. Don’t you worry, Serena, I got your message and I will surely be thinking about that after our date.**

SERENA: Okay.

DAN: Say, it's a nice place that you’ve got here.

**You don’t belong here, Serena. You are not like your mother or Blair or Nate or Chuck – you are so much more than your wealth. You deserve so much better than this hotel room, not matter how lavish it is. You, Serena, deserve a home. One that you and I can make, together. You just have to trust me and see that you belong with me. You and me, Serena – we can start our own little world, together. One without the judgement and the pressure. Without your mother and definitely without Blair. You and I will be inseparable, an unbreakable team, you will understand me, know me, and I will know all of you. You’ll see.**

SERENA: Yeah, the, uh, identical surroundings do make you crazy after a little while.  
Sometimes I feel like I'm in a secret government experiment.

DAN: Most government experiments don't have plasma TVs or maid services.  
Just something I've noticed.

**You are so witty – so much funnier than anyone has ever given you credit for.**

[LILY ENTERS THE ROOM, SHOPPING BAGS IN HAND]

LILY: Dan. Does Serena know you're here? 

**“Does Serena know you’re here?” Of course she does, Lily. That’s one thing you and I will have to deal with, Serena, your overbearing mother. She doesn’t really care about you. She would rather go out and spend thousands of dollars on herself than spend the afternoon with you. But not me, Serena. When I am not with you, all I think about is you. You completely consume me. I hate your mother, though. Did you hear the way that she belittled me? Made it clear that she does not think I’m worthy of you? If I have to, I’ll work forever until I can prove to her that I am exactly what you need.**

DAN: Yeah, of course. She let me in. At least, I hope that was her. She's about, uh, yea tall and very blonde? 

LILY: It makes jokes. Cute.

**Cute. CUTE! Can you believe your mother would call me “cute,” like I’m a stuffed-animal. Or a baby. No, Serena, your mother will not get away with embarrassing me like this in front of you.**

DAN: Big shopping day? 

LILY: I had a lot on my mind. So where are you taking my daughter tonight? 

**A lot on her mind, and I bet none of it was you.**

DAN: I, I don't know. I thought maybe we'd do a walking tour of New York underground, visit my friends the mole people. They're great, except they only ever eat leftovers.  
I'm sorry.  
I don't know why I just said any of that.  
I have--I have this thing, this nervous tic where I never stop speaking, like, ever.  
In fact, when I was a little boy, my mom used to say there was never a word I met that I didn't like.  
You know what else I like? Your daughter.  
I-I really like your daughter.

**I spiral. I get lost in my words. But you, the sight of you brings me back down to earth.**

[SERENA ENTERS WEARING AN EXPENSIVE-LOOKING BLACK DRESS AND A BROWN HOBO BAG]

DAN: I Wow.

LILY: You're not wearing that with that, are you? 

**She is so critical of you.**

SERENA: Uh, mom.

LILY: Wait.  
Take this.

[LILY HANDS SERENA A BLACK HANDBAG]

SERENA: Oh, thank you.

**You look at me. I am a sense of comfort for you. You look at me and you know I see you for all that you are. You take my hand. You have to notice how perfectly your hand fits in mine.**

SERENA: Come on.  
Let's go.

[DAN AND SERENA WALK OUTSIDE TO THE STREET] 

**Oh, Serena. I can’t wait for you to see the chariot we have waiting for us. I rented it myself. You can’t even begin to understand how many calls it took before someone finally took me seriously. But you, you always take me seriously.**

SERENA: Oh, my god, a vespa! I can't believe it! I love vespas! Oh, my gosh.  
You don't understand.  
I spent one of my favorite summers riding all around Italy on one of these.

**Shit. No, Serena, you don’t understand. I didn’t rent this vespa for us – how would I have known? Your MySpace page and bio on Gossip Girl never said anything about your affinity for tiny, Italian motor bikes. I should’ve known. I should’ve guessed. You should’ve told me. Now you’ve made me look like an idiot, but I’ll forgive you, Serena. You had no idea that I was capable of fitting into your world so well.**

SERENA: How did you know? My mom won't let me learn to drive 'cause she says that's what drivers are for, But really, Dan, this is amazing.  
Really.  
[SERENA GRABS DAN'S ARM AND PLAYFULLY SHAKES IT]  
Come on.  
Where are the helmets? 

**I don’t even know what to say.**

[DRIVER STANDS IN FRONT OF A BLACK CAR]

DRIVER: Mr. Humphrey.

SERENA: Is he--Is he ours? 

DAN: Yeah.

SERENA: Okay, great.

[DAN AND SERENA GET IN THE CAR AND DRIVE OFF]

**Serena, I’m going to do better, I promise. I know you, believe me. I know what you like and the type of date you deserve to go on. You are worth every penny that I am spending on you tonight. And let me tell you, it’s a whole hell of a lot of pennies. But I do it for you. You are everything to me, and I can’t wait to show you that I can be everything to you, too, if you just trust me.**  
[SERENA AND DAN SIT AT A TABLE IN AN EXPENSIVE RESTAURANT]

**I want to impress you, Serena. I don’t want you to be embarrassed of me, a lonely boy from Brooklyn. I can fit in to your world. This dinner is my first step in proving that to you.**

DAN: Um, how's the braised quail? 

WAITER: Very good, sir.  
.  
DAN: And the, uh, the lay-Pin? 

WAITER: Lah-Pan.  
It's delightful.

**I can’t believe he corrected me like that, trying to make me look like a fool. And in front of you! I’ll bite my tongue.**

DAN: Okay, what is that again? 

WAITER: Rabbit, sir.

DAN: Oh, well, I won't be having that.  
Um, how about chicken? You can't go wrong with chicken.

WAITER: Yes, sir.

DAN: Thank you.

WAITER: Miss? 

SERENA: Uh, I'll have the lobster bisque and muscovy duck, please.  
Thank you.

WAITER: Merci, mademoiselle.

**You even make the food you order sound so perfect. Of course you deserve a bisque, not soup, and duck, not chicken. This waiter, though, is a problem. He is doing his best to make you think that I don’t belong here with you.**

DAN: I can't believe the waiter forgot me.  
I was--I was just here the other day.  
Yeah, I come here for the crowd.  
You wanna play "mistress or second wife"? Because it's harder than it looks.  
Believe me.

SERENA: Uh, will you excuse me? I, uh I'm gonna go to the restroom to freshen up a little.

DAN: Yeah, of course, of course.  
I think the bathrooms are—

SERENA: Uh, don't worry.  
I'll find them.

[SERENA LEAVES THE TABLE TO GO TO THE RESTROOM AND MAKES A PIT STOP BY THE REGISTER TO PAY FOR DINNER HERSELF]

**You don’t even need to freshen up, Serena. I’ll take you however you come to me. But, I am worried about being able to pay for your fancy soup and upgraded bird.**

[DAN SIGNALS TO THE WAITER]

DAN: Oh, excuse me, sir.  
Uh, how much is that duck she just ordered? 

WAITER: $78, sir.

**Holy shit, Serena. I knew your world was luxurious, but $78 for just one part of your meal? I’m going to have to get a job to keep up with you.**

DAN: Okay, right.  
Thank you.  
Um, you know what? Can you just cancel my main dish, And I'll just have the appetizer as the main?

**That’s what I do for you, Serena. I make sacrifices so that you can have exactly what you want.**

WAITER: Of course, sir.

[SERENA RETURNS, THEY RECEIVE THEIR DINNER AND FINISH THEIR MEAL]

SERENA: Are you sure you didn't want any of my dinner? Your entrée was so small.

DAN: No, no, no, no.  
It was amazing.  
I didn't realize, uh, fish could be creamed.

**DISGUSTING. I want nothing more than to eat what’s on your plate – you didn’t even touch half of your duck.**

WAITER: Would you like to see the dessert menu? 

SERENA: Oh, no, thank you.  
I think we're fine.

DAN: Sure you don't want dessert? 

SERENA: Yeah.

DAN: Okay, well, then we'll just get the check, please.

SERENA: Uh, actually I already took care of that earlier.

DAN: What? 

**I’m sorry, what?**

SERENA: Mm-Hmm.  
Yeah, I-I just charged it on my mom's card.  
It's--It's not a big deal.  
Don't worry about it.

DAN: You know, I can pay.  
It's not like I don't have the money.

SERENA: Yeah, I'm--I'm sure you do.  
You just shouldn't have to spend it here.

DAN: I don't understand.  
Did I do something wrong? 

**Serena, what are you doing to me? Are you worried that I wasn’t going to be able to pay for all of this? I used money I’d been saving up for years on my date with you. Of course I have enough money. Why would you belittle me like that? Or, is this just an example of how giving you are? You saw my need, and you met it without even batting an eye. You really are something. But still, I need to know why.**

SERENA: No.  
Look, I wanted a date with you, just not the date you thought I wanted.  
It's--It's fine.

**With me? The real me? Serena. This may be too soon, but I just know. I. Love. You. You see me, you understand me, you want to know more about me. I’m going to do everything in my power for you to feel the same love for me that I feel for you. Although, I think you already do.**

DAN: All right, all right.  
Well, then if it's a real Dan Humphrey date that you want, then it's a real Dan Humphrey date that you're gonna get.  
Let's go.

SERENA: Really?

DAN: Yes.  
Mademoiselle.

[DAN OFFERS HIS ARM, SERENA TAKES IT, AND THE TWO WALK THROUGH THE STREETS OF MANHATTAN.]


End file.
